“So, what is this “casually dating” that you speak of?” a married male friend asked. I had made an off the cuff comment about some mutual friends who needed to learn how to casually date. But, when he asked the question, I realized I didn’t really have a good answer. “I think that’s great blog fodder,” I said. I mean, I know what I mean by casually dating. I mean I date different men to get to know them better and see if any of them are relationship material. In my mind, we do fun things together like hike, go out to dinner, and whatever else that we both like to do.

But, then it gets pretty murky. Of course, it always gets murky when you think about whether or not sex is involved. At least when I was young, I knew I wasn’t supposed to have sex, so that made it something that at least had to be delayed a bit and/or alcohol had to be involved. So, I did what I always do, I googled Casual Dating. Interestingly enough, one website said that casual dating was dating a variety of people with no immediate intention of having a relationship and sexual activity was usually not involved. Another one said that it is basically the same as “friends with benefits” which means that you can date different people but you also have sex with this person – no strings attached. These same two opinions were mirrored by my friends. My gay friend JD (not his real name) said that in the gay community it may or may not mean sex. One of my girlfriends, I’ll call her Tina, said immediately that it was the same as “friends with benefits.” In her words, “I went right to that when you said it.”

It seems like this is such a subtle difference, and you just have to find someone else who is on the same page around sex. However, in practice, this is just not that easy. For one thing, does anybody ever really know if they are going to want a relationship with a person ahead of time? Sure, it sounds good…..but, often those missing strings come back to strangle you and the friendship. I’ve had many friendships where I either fell in love with the guy eventually, or he fell in love with me, and the friendship ended. These didn’t even involve sex. Are you going to tell me that if we get naked together, that’s not going to happen? Hmmmm….maybe….maybe not??

Women have more difficulty with this than men. In both genders, the hormone oxytocin is released during sexual activity and is responsible for bonding between two partners. As with anything else, the amount released and the impact of this hormone on any individual can vary. So, do you ask someone beforehand, what is your typical reaction to the hormone oxytocin when you have sex? I mean, if I’m going to have sex and am counting on not wanting to be in a relationship with them, I need to be honest with myself and I’d like to know how they will react. I don’t want to have to hurt somebody just because we really didn’t know what we were doing. And, this is the thing, there is nothing wrong with you if you can have casual sex and walk away from it, and there is nothing wrong with somebody who can’t. It’s just another difference in people. And, by the age of 50, if you don’t know which category you fall into, well, you might need a therapist.

My friend, Rachel (name is changed because I’d like her to be my friend after this is published) said her counselor told her emphatically, ” You SUCK at casual dating.” Well…. I asked her, what did he mean by casual dating? Her take was that casual dating meant doing fun things together with the intention of getting to know each other and not really heading toward a relationship. She said, for her, that definitely meant sex was out. She just can’t have sex and not start developing feelings for somebody. I have to say I’m in the same camp. And, it’s made dating more complicated for several reasons.

My first issue is that I don’t really know if I want to get into another long term relationship. I think I do, but, with two failed marriages behind me, I’m just not sure if I’m capable of it or if I want to commit again. I really love my single life, and it is pretty full. I do wish that I had someone to do things with and, yes, even be intimate. But, it’s so hard when you are navigating that dating world. I’ve met men I like, and I’d like to get to know them, but, like Billy Crystal said in Harry Met Sally, the sex always gets in the way. At some point, I have to decide where I’m going with that. And that complicates things. And, I’m an adult; I don’t want to wait that long.

The other thing that I’ve learned throughout my years of therapy is that when you introduce sex into a relationship, the emotional bonding is halted. It feels like it is still growing, but, in reality, its a sexual bond. And that bond can cause you to miss some very key things with a partner in trying to determine if they are right for you. And, if you don’t bond emotionally, the bond is very fragile. I told a counselor that I just didn’t know that I could do without that part of a romantic partnership, and he suggested that I just wait as long as I could before having sex. He said the longer you wait, the more bonded you will be. That is so easy in theory.

I’ve approached dating in the last two years as casually as I could. I’ve met a lot of men and dated a handful more than a couple of times. But, I’ve not been in a long-term relationship yet or even a short term one. I read a book called, “How to Get a Date Worth Keeping” by Dr. Henry Cloud two years ago. He advocates the style of dating that I’ve been doing. You meet a lot of people of the opposite sex, and do some fun things with them with no intention of getting married. You sort of treat it as a “numbers” game. As you meet people, you will determine what kind of person you like, and you’ll make better choices in partners. So, I’ve been finding out what I like. I’ve also learned a lot about myself. I’ve learned what type of person I don’t like – addicted, emotionally unavailable, avoidant, controlling, etc. (uh oh….that describes my ex) – and I’ve learned how to spot them more quickly. I jokingly call one of my friends “my dating coach”. I’m joking, but not really. She helps keep me sane because, even though I don’t like some of the types for me, I’m still very attracted to them. It doesn’t make sense, but it happens, and I have to pull myself away when I don’t want to because I know that it’s not good for me in the end. I’ve starred in that movie before, and it doesn’t end well for me.

I’ve also learned how to reject people with kindness, and I’ve learned how to take rejection without taking it personally. Somebody just rejected me 20 minutes ago. It’s not personal. He doesn’t even know me. It’s about him and what he’s looking for. And I really respect a man that will tell you instead of just disappearing. He was that kind. I’ve learned that men are really sweet people. I’ve had numerous ones open up to me about their fears around rejection and how powerful those are. I’ve dated men that had been in long term marriages and were so nervous that their hands were shaking. I met over 50 men in the last 2 years dating online. Some are my friends now. Some are engaged to other people. I fixed a couple of them up with my friends because I thought they were a good match. A few of them were crazy, but only a few. For the most part, they were very nice and a lot of fun. Casual dating for me is just that. It’s casual. It’s not going anywhere special or feeling like I have to dress up to get there OR take my clothes off. But, whatever it is, it’s still dating, and that makes it inherently complicated.